Hydrochloric Acid → HCID 178456037, compound

HRID 1405311Notes

Reaction equation

[C@H:1]([N:5]([CH3:25])[C:6]1[C:7]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]#[N:17])=[CH:11][CH:10]=2)([CH2:3][CH3:4])[CH3:2].[N-:26]=[N+:27]=[N-:28].[Na+].Cl>CS(C)=O.O.[Zn+2].[Br-].[Br-]>[C@H:1]([N:5]([CH3:25])[C:6]1[C:7]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[N:8][C:9]2[C:14](=[CH:13][C:12]([C:16]3[NH:28][N:27]=[N:26][N:17]=3)=[CH:11][CH:10]=2)[N:15]=1)([CH2:3][CH3:4])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of (R)-3-(sec-butyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carbonitrile (170 mg, 0.51 mmol) in DMSO (25 mL) was added NaN3 (101 mg, 1.55 mmol), ZnBr2 (56 mg, 0.25 mmol) and water (3 mL) and the resulting mixture was stirred overnight at 130° C. The solution was diluted with water (200 mL) and adjusted to pH 4 with HCl (3N), extracted with ethyl acetate (5×50 mL), and the organic layers combined and dried over anhydrous magnesium and concentrated in vacuo to afford (R)—N-sec-butyl-3-(4-fluorophenyl)-N-methyl-7-(1H-tetrazol-5-yl)quinoxalin-2-amine as a yellow solid (72.3 mg, 37%).

Workup

extractionextracted with ethyl acetate (5×50 mL)
dry with materialdried over anhydrous magnesium
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6f6331c22c9e462c85b68cafd5134840
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916561B2

Reaction notes

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